Method for the Synthesis of Phenothiazines via a Domino Iron-Catalyzed C–S/C–N Cross-Coupling Reaction

Abstract

An environmentally benign and efficient method has been developed for the synthesis of phenothiazines via a tandem iron-catalyzed C-S/C-N cross-coupling reaction. Some of the issues typically encountered during the synthesis of phenothiazines in the presence of palladium and copper catalysts, including poor substrate scope, long reaction times and poor regioselectivity, have been addressed using this newly developed iron-catalyzed method.

Evaluating Nitrogen-Containing Biosynthetic Products Produced by Saltwater Culturing of Several California Littoral Zone Gram-Negative Bacteria

“…Key insights to guide the next steps of the structure determination came from additional hits observed during literature searches for compounds with similarity to 1 using atom counts of C 10–14 N 2 S. The hit list included (a) C 12 H 10 N 2 S (U# = 9), a synthetic compound we named 3-methylbenzopyridothiazine ( 2 ), 19 and (b) C 14 H 14 N 2 SO 2 (U# = 9), a bryzoan metabolite 1-ethyl-4-methylsulfone- β -carboline ( 3 ). 20 Also relevant to this set is 1-methyl- β -carboline (aka harman) ( 4 ), 21 a plant metabolite.…”

Research Progress of Phenothiazine Compounds of Dioxopromethazine Hydrochloride

“…In 1883, the German chemist Bernthsen reported on the synthesis of phenothiazine using diphenylamine and sulfur as the reaction substrates under high temperature conditions. This is the first time that the phenothiazine synthesis method has been reported [14]. For many years to come, this traditional route was the dominant method for the synthesis of phenothiazines.…”

Copper(II) Complex Supported on Fe3O4@SiO2 Coated by Polyvinyl Alcohol as Reusable Nanocatalyst in N‐Arylation of Amines and N(H)‐ Heterocycles and Green Synthesis of 1H‐Tetrazoles

“…In the past decades, the transition metal catalyzed formation of C‐heteroatom bonds has been interest of many researches due to their high efficiency, economic viability, and stability in air . These kinds of cross‐couplings reactions are unique method for the production of many biologically and pharmaceutically important molecules . There are many reports in the literature based on using palladium or supported palladium on magnetic nanoparticles,, molybdenum, nickel, iron, cobalt, and copper in the C−X (X=O, N, S) couplings.…”

“…[23] These kinds of cross-couplings reactions are unique method for the production of many biologically and pharmaceutically important molecules. [24] There are many reports in the literature based on using palladium or supported palladium on magnetic nanoparticles, [25,26] molybdenum, [27] nickel, iron, cobalt, and copper [25] in the CÀX (X=O, N, S) couplings. The copper mediated processes, such as Ullmann and Ullmann-like reactions, have been among the most popular attractive general methods for CÀC, CÀN, and CÀO bond formations in aryl couplings.…”